NP-MRD: Showing NP-Card for chebulanin (NP0039540)

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Record Information

Version

2.0

Created at

2021-06-20 21:56:33 UTC

Updated at

2021-06-30 00:12:56 UTC

NP-MRD ID

NP0039540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chebulanin

Provided By

JEOL Database JEOL Logo

Description

chebulanin is found in Terminalia bellerica, Terminalia chebula and Terminalia horrida. chebulanin was first documented in 2010 (Pfundstein, B., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123563D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202123563D          

 70 74  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0039540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@]1([H])C(=O)O[C@]2([H])[C@]([H])(O[H])[C@]([H])(OC(=O)C3=C4C(OC(=O)[C@@]([H])(O[H])[C@@]14[H])=C(O[H])C(O[H])=C3[H])[C@]([H])(OC(=O)C1=C([H])C(O[H])=C(O[H])C(O[H])=C1[H])O[C@]2([H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O19/c28-5-12-20-19(37)22(27(42-12)46-23(38)6-1-9(29)16(34)10(30)2-6)45-24(39)7-3-11(31)17(35)21-15(7)14(18(36)26(41)44-21)8(4-13(32)33)25(40)43-20/h1-3,8,12,14,18-20,22,27-31,34-37H,4-5H2,(H,32,33)/t8-,12+,14-,18-,19-,20-,22-,27-/m0/s1

> <INCHI_KEY>
HPQIRFXIDGVWBA-PTDBXSLJSA-N

> <FORMULA>
C27H24O19

> <MOLECULAR_WEIGHT>
652.47

> <EXACT_MASS>
652.091178553

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.55653333972316

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4S,5S,7R,8R,11S,12S,13S,21S)-13,17,18,21-tetrahydroxy-7-(hydroxymethyl)-2,10,14-trioxo-5-(3,4,5-trihydroxybenzoyloxy)-3,6,9,15-tetraoxatetracyclo[10.7.1.1^{4,8}.0^{16,20}]henicosa-1(20),16,18-trien-11-yl]acetic acid

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
-0.1468243773333332

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.865244612441627

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2245098465656166

> <JCHEM_PKA_STRONGEST_BASIC>
-3.708943032388949

> <JCHEM_POLAR_SURFACE_AREA>
313.57

> <JCHEM_REFRACTIVITY>
139.4481

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4S,5S,7R,8R,11S,12S,13S,21S)-13,17,18,21-tetrahydroxy-7-(hydroxymethyl)-2,10,14-trioxo-5-(3,4,5-trihydroxybenzoyloxy)-3,6,9,15-tetraoxatetracyclo[10.7.1.1^{4,8}.0^{16,20}]henicosa-1(20),16,18-trien-11-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 74  0  0  0  0  0  0  0  0999 V2000
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    0.3955    2.4627    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4309    2.7780    1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2898    4.4874    0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9666    3.0737   -0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7577    4.2734   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 36  1  0
 11 12  1  0
 31 29  1  0
 29 28  1  0
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 37 35  2  0
 39  5  1  0
 27 45  1  0
  5  4  1  0
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 45  9  1  0
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 33 32  2  0
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  3 47  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       2.019   1.341  -4.555  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.884   2.348  -3.878  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.330   3.481  -4.362  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.253   2.426  -2.414  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.108   1.914  -1.531  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.134   2.701  -1.903  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.199   3.922  -1.968  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.157   1.853  -2.149  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.498   2.391  -2.138  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.433   1.299  -2.698  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.057   0.916  -4.133  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.187   2.043  -4.990  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.376   0.111  -1.889  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.786   0.328  -0.528  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.667  -0.921   0.167  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.448  -1.040   1.264  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.321  -0.258   1.605  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.078  -2.256   2.037  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.816  -2.549   3.199  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.458  -3.643   3.979  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.135  -3.975   5.119  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.370  -4.431   3.621  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.997  -5.498   4.392  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.637  -4.139   2.479  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.542  -4.892   2.161  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.993  -3.069   1.669  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.907   1.400   0.159  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.523   0.941   0.219  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.109   0.359   1.356  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.769   0.176   2.364  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.273  -0.158   1.185  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.471  -1.456   1.696  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.728  -2.040   1.651  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.942  -3.312   2.102  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.811  -1.324   1.160  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.052  -1.893   1.172  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.627  -0.030   0.679  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.356   0.566   0.632  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.272   1.960   0.032  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.474   2.740   0.581  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.419   4.090   0.129  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.793   2.057   0.230  0.00  0.00           C+0
HETATM   43  O   UNK     0       4.799   2.699  -0.062  0.00  0.00           O+0
HETATM   44  O   UNK     0       3.778   0.674   0.267  0.00  0.00           O+0
HETATM   45  C   UNK     0      -2.942   2.684  -0.687  0.00  0.00           C+0
HETATM   46  O   UNK     0      -2.146   3.689  -0.046  0.00  0.00           O+0
HETATM   47  H   UNK     0       1.181   4.185  -3.694  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.151   1.813  -2.289  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.541   3.458  -2.196  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.920   0.874  -1.837  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.534   3.299  -2.751  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.465   1.674  -2.701  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.718   0.122  -4.496  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.032   0.533  -4.189  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.827   1.779  -5.856  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.836   0.646  -0.559  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.649  -1.910   3.481  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.845  -3.321   5.258  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.645  -5.502   5.128  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.554  -5.621   2.817  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.410  -2.865   0.776  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.259   1.620   1.174  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.362  -1.996   2.136  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.076  -3.725   2.289  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.921  -2.789   1.542  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.396   2.463   0.459  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.431   2.778   1.677  0.00  0.00           H+0
HETATM   68  H   UNK     0       3.290   4.487   0.335  0.00  0.00           H+0
HETATM   69  H   UNK     0      -3.967   3.074  -0.704  0.00  0.00           H+0
HETATM   70  H   UNK     0      -1.758   4.273  -0.729  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    3    1                                                  
CONECT    3    2   47                                                       
CONECT    4    5    2   48   49                                             
CONECT    5   39    4    6   50                                             
CONECT    6    5    8    7                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9   45   10    8   51                                             
CONECT   10    9   13   11   52                                             
CONECT   11   12   10   53   54                                             
CONECT   12   11   55                                                       
CONECT   13   10   14                                                       
CONECT   14   13   27   15   56                                             
CONECT   15   16   14                                                       
CONECT   16   18   15   17                                                  
CONECT   17   16                                                            
CONECT   18   19   26   16                                                  
CONECT   19   18   20   57                                                  
CONECT   20   19   22   21                                                  
CONECT   21   20   58                                                       
CONECT   22   20   24   23                                                  
CONECT   23   22   59                                                       
CONECT   24   22   26   25                                                  
CONECT   25   24   60                                                       
CONECT   26   24   18   61                                                  
CONECT   27   45   14   28   62                                             
CONECT   28   29   27                                                       
CONECT   29   31   28   30                                                  
CONECT   30   29                                                            
CONECT   31   29   32   38                                                  
CONECT   32   33   31   63                                                  
CONECT   33   35   32   34                                                  
CONECT   34   33   64                                                       
CONECT   35   36   37   33                                                  
CONECT   36   35   65                                                       
CONECT   37   35   38   44                                                  
CONECT   38   31   37   39                                                  
CONECT   39    5   38   40   66                                             
CONECT   40   41   39   42   67                                             
CONECT   41   40   68                                                       
CONECT   42   43   40   44                                                  
CONECT   43   42                                                            
CONECT   44   37   42                                                       
CONECT   45   27    9   46   69                                             
CONECT   46   45   70                                                       
CONECT   47    3                                                            
CONECT   48    4                                                            
CONECT   49    4                                                            
CONECT   50    5                                                            
CONECT   51    9                                                            
CONECT   52   10                                                            
CONECT   53   11                                                            
CONECT   54   11                                                            
CONECT   55   12                                                            
CONECT   56   14                                                            
CONECT   57   19                                                            
CONECT   58   21                                                            
CONECT   59   23                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   32                                                            
CONECT   64   34                                                            
CONECT   65   36                                                            
CONECT   66   39                                                            
CONECT   67   40                                                            
CONECT   68   41                                                            
CONECT   69   45                                                            
CONECT   70   46                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  148    0
END

RDKit          3D

70 74  0  0  0  0  0  0  0  0999 V2000
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   -3.4332    1.2989   -2.6978 C   0  0  1  0  0  0  0  0  0  0  0  0
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 37 44  1  0
 42 43  2  0
 38 39  1  0
 40 41  1  0
 39 40  1  0
  5 50  1  6
 40 42  1  0
  4  2  1  0
 42 44  1  0
  2  3  1  0
 45 46  1  0
  2  1  2  0
 33 34  1  0
 39 66  1  1
  8  9  1  0
 40 67  1  1
 12 55  1  0
 11 53  1  0
 11 54  1  0
 46 70  1  0
 27 62  1  1
 10 52  1  6
 14 56  1  6
  9 51  1  6
 45 69  1  6
 32 63  1  0
 34 64  1  0
 36 65  1  0
  4 48  1  0
  4 49  1  0
 19 57  1  0
 26 61  1  0
 21 58  1  0
 23 59  1  0
 25 60  1  0
 41 68  1  0
  3 47  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₄O₁₉

Average Mass

652.4700 Da

Monoisotopic Mass

652.09118 Da

IUPAC Name

2-[(4S,5S,7R,8R,11S,12S,13S,21S)-13,17,18,21-tetrahydroxy-7-(hydroxymethyl)-2,10,14-trioxo-5-(3,4,5-trihydroxybenzoyloxy)-3,6,9,15-tetraoxatetracyclo[10.7.1.1^{4,8}.0^{16,20}]henicosa-1(20),16,18-trien-11-yl]acetic acid

Traditional Name

[(4S,5S,7R,8R,11S,12S,13S,21S)-13,17,18,21-tetrahydroxy-7-(hydroxymethyl)-2,10,14-trioxo-5-(3,4,5-trihydroxybenzoyloxy)-3,6,9,15-tetraoxatetracyclo[10.7.1.1^{4,8}.0^{16,20}]henicosa-1(20),16,18-trien-11-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@]1([H])C(=O)O[C@]2([H])[C@]([H])(O[H])[C@]([H])(OC(=O)C3=C4C(OC(=O)[C@@]([H])(O[H])[C@@]14[H])=C(O[H])C(O[H])=C3[H])[C@]([H])(OC(=O)C1=C([H])C(O[H])=C(O[H])C(O[H])=C1[H])O[C@]2([H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C27H24O19/c28-5-12-20-19(37)22(27(42-12)46-23(38)6-1-9(29)16(34)10(30)2-6)45-24(39)7-3-11(31)17(35)21-15(7)14(18(36)26(41)44-21)8(4-13(32)33)25(40)43-20/h1-3,8,12,14,18-20,22,27-31,34-37H,4-5H2,(H,32,33)/t8-,12+,14-,18-,19-,20-,22-,27-/m0/s1

InChI Key

HPQIRFXIDGVWBA-PTDBXSLJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Terminalia bellirica	JEOL database	Pfundstein, B., et al, Phytochem. 71, 1132 (2010)
Terminalia chebula	JEOL database	Pfundstein, B., et al, Phytochem. 71, 1132 (2010)
Terminalia horrida	JEOL database	Pfundstein, B., et al, Phytochem. 71, 1132 (2010)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.88	ALOGPS
logP	-0.15	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.22	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	313.57 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.45 m³·mol⁻¹	ChemAxon
Polarizability	57.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Pfundstein, B., et al. (2010). Pfundstein, B., et al, Phytochem. 71, 1132 (2010). Phytochem..

Showing NP-Card for chebulanin (NP0039540)

MOL for NP0039540 (chebulanin)

3D MOL for NP0039540 (chebulanin)

3D SDF for NP0039540 (chebulanin)

3D-SDF for NP0039540 (chebulanin)

PDB for NP0039540 (chebulanin)

3D PDB for NP0039540 (chebulanin)

SMILES for NP0039540 (chebulanin)

INCHI for NP0039540 (chebulanin)

Structure for NP0039540 (chebulanin)

3D Structure for NP0039540 (chebulanin)